US3954846A - New quaternary ammonium salts of malic acid and their application in cosmetics - Google Patents
New quaternary ammonium salts of malic acid and their application in cosmetics Download PDFInfo
- Publication number
- US3954846A US3954846A US05/535,713 US53571374A US3954846A US 3954846 A US3954846 A US 3954846A US 53571374 A US53571374 A US 53571374A US 3954846 A US3954846 A US 3954846A
- Authority
- US
- United States
- Prior art keywords
- malate
- quaternary ammonium
- malic acid
- malic
- cosmetics
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 title claims abstract description 44
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical class OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 title claims abstract description 13
- 239000001630 malic acid Substances 0.000 title claims abstract description 13
- 235000011090 malic acid Nutrition 0.000 title claims abstract description 13
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 12
- 239000002537 cosmetic Substances 0.000 title abstract description 8
- 229940049920 malate Drugs 0.000 claims description 31
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 claims description 10
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 claims description 5
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 claims description 5
- QDYLMAYUEZBUFO-UHFFFAOYSA-N cetalkonium chloride Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 QDYLMAYUEZBUFO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000002500 ions Chemical class 0.000 abstract description 10
- -1 aliphatic hydrocarbon radical Chemical class 0.000 abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 5
- 239000006071 cream Substances 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- 230000003834 intracellular effect Effects 0.000 abstract description 4
- 230000035515 penetration Effects 0.000 abstract description 4
- 230000019522 cellular metabolic process Effects 0.000 abstract description 3
- 150000005840 aryl radicals Chemical class 0.000 abstract description 2
- 239000008271 cosmetic emulsion Substances 0.000 abstract description 2
- 229920006395 saturated elastomer Polymers 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 24
- 239000007864 aqueous solution Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- UKHWJBVVWVYFEY-UHFFFAOYSA-M silver;hydroxide Chemical compound [OH-].[Ag+] UKHWJBVVWVYFEY-UHFFFAOYSA-M 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 235000019658 bitter taste Nutrition 0.000 description 4
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 230000009965 odorless effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229960000907 methylthioninium chloride Drugs 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000004313 potentiometry Methods 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
- 101001022148 Homo sapiens Furin Proteins 0.000 description 1
- 101000701936 Homo sapiens Signal peptidase complex subunit 1 Proteins 0.000 description 1
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241000083869 Polyommatus dorylas Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 102100030313 Signal peptidase complex subunit 1 Human genes 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- KQPMUAVPQFOWOM-CYVLTUHYSA-N [(7z)-1,1,4a,8-tetramethyl-7-[2-[2-(methylamino)ethoxy]-2-oxoethylidene]-9-oxo-2,3,4,4b,5,6,8,8a,10,10a-decahydrophenanthren-2-yl] 3-methylbut-2-enoate Chemical compound CC1(C)C(OC(=O)C=C(C)C)CCC2(C)C3CC/C(=C/C(=O)OCCNC)C(C)C3C(=O)CC21 KQPMUAVPQFOWOM-CYVLTUHYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001532 anti-fungicidal effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000021302 avocado oil Nutrition 0.000 description 1
- 239000008163 avocado oil Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229960000228 cetalkonium chloride Drugs 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- JZKFHQMONDVVNF-UHFFFAOYSA-N dodecyl sulfate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCCCCCCOS(O)(=O)=O JZKFHQMONDVVNF-UHFFFAOYSA-N 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- WJLUBOLDZCQZEV-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)C WJLUBOLDZCQZEV-UHFFFAOYSA-M 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- XYQREBYZFVVGCJ-UHFFFAOYSA-N icosan-10-ol Chemical compound CCCCCCCCCCC(O)CCCCCCCCC XYQREBYZFVVGCJ-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229940031957 lauric acid diethanolamide Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UWTATZPHSA-M malate ion Chemical compound [O-]C(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-M 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
- 239000011619 pantothenol Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229930195732 phytohormone Natural products 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YXZRCLVVNRLPTP-UHFFFAOYSA-J turquoise blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].NC1=NC(Cl)=NC(NC=2C=C(NS(=O)(=O)C3=CC=4C(=C5NC=4NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)NC=4NC(=C6C=C(C=CC6=4)S([O-])(=O)=O)NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)N5)C=C3)C(=CC=2)S([O-])(=O)=O)=N1 YXZRCLVVNRLPTP-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Definitions
- R is a monovalent aliphatic hydrocarbon radical, saturated or unsaturated, of 8 to 20 carbon atoms, preferably of 12 to 18 carbon atoms;
- R 1 , R 2 , R 3 may be identical or different and each represents a lower alkyl radical of at most 4 carbon atoms, or an aryl radical.
- R is the lauryl, myristyl, cetyl or aleyl radical, and R 1 , R 2 R 3 each designate a methyl, ethyl, propyl, isopropyl, phenyl or benzyl radical.
- the quaternary ammonium salts of malic acid may be prepared by reaction of maleic acid with the corresponding hydroxide of the quaternary ammonium salt: ##EQU3## in aqueous medium in the presence of ethanol or isopropanol.
- the corresponding hydroxide of the quaternary ammonium salt may be prepared in situ by reaction of the corresponding halide of the quaternary ammonium salt with an excess of silver hydroxide, preferably freshly prepared.
- the new quaternary ammonium salts of malic acid of this invention are especially useful in cosmetics. It is known that malic acid is one of the fundamental factors in cellular metabolism, and as such it presents considerable interest in cosmetics, especially in the manufacture of cleansing creams.
- malic acid cannot be used in the free state or neutral state without certain precautions, because it interferes as an electrolyte and, in reducing the stability of the emulsions, it can lead to break-up of the emulsion.
- the electric conductivity of the aqueous phase of the emulsion increases, the electrostatic charges on the particles of the oily phase in suspension are reduced. This causes a lowering of the forces of repulsion which may thus become less than the Van der Waals forces of attraction, and this inevitably leads to the break-up of the emulsion.
- fat-soluble esters of malic acid be used in place of the said acid to achieve a better intracellular penetration of malic ion. Nevertheless, these esters have a tendency to hydrolyze in aqueous solution, which affects the stability of cosmetic emulsions. Moreover, they are not surface-active, and are neither bactericidal nor anti-fungicidal.
- the quaternary ammonium salts of malic acid of this invention are particularly valuable for the care of the skin in general, and especially in cosmetics, for the following reasons:
- This malic ion penetrates the skin rapidly through the sebum, thanks to the lipophilic quaternary ammonium ion to which it is in polarly bonded.
- these substances being water-soluble, may be used in aqueous solution, for example in hair lotions.
- Silver nitrate (600 g) is dissolved in purified water (2.5 liters).
- the pH of an aqueous solution to 1/5 strength should be near 6.
- the mixture is concentrated to about 3 liters by distillation of ethanol, then evaporated to dryness under vacuum (60°C, 15 mm Hg).
- the cetyltrimethylammonium malate is obtained as a white mass of waxy consistency, soluble in water and alcohols, insoluble in petroleum ether, benzene and cyclohexane.
- composition cetylmethylammonium ion: 81.17%
- Absolute ethanol was added to break up the foam which would make concentration impossible; ethanol may be replaced by smaller quantities (about 1 liter) of isopropanol.
- silver hydroxide may be avoided by using anion exchangers of the polystyrene/quaternary ammonium type (for example, Amberlite I R A 400) to fix the chlorine.
- anion exchangers of the polystyrene/quaternary ammonium type for example, Amberlite I R A 400
- cetyltrimethylammonium malate is applied in aqueous solution (25% w/w).
- the pH of the solution is near 6.
- test mixture above is boiled vigorously. A rancid odor, characteristic of fatty alcohols, develops.
- the sumagent alcohol is separated: M.P. 49°C.
- the mixture is stirred until all is dissolved (about 30 minutes), and the volume made up to 1000 ml with water.
- VS blue (0.2 mg/ml, 5 ml)
- VS blue (CI 42045) is the sodium salt of [[ ⁇ -[p-(dimethylamino)phenyl]-disulphobenzylidene-2,4]-4cyclohexadiene-2.5-ylidine-1]diethylammonium) ##SPC1##
- the upper solvent phase is colored turquoise blue, whereas there is almost no coloration in a control solution containing no cetyltrimethylammonium malate.
- cetyltrimethylammonium malate solutions may be titrated by potentiometry in an anhydrous acetic medium as follows:
- malate solution (approx. 1 g) weighed to an accuracy of 0.1 mg.
- Anhydrous acetic acid (R) 80 ml is added, and the solution is concentrated at atmospheric pressure down to about 40 ml to remove water by azeotropy.
- V volume (ml) of perchloric acid consumed
- M molecular weight of cetyltrimethylammonium malate: 701.25
- Example 2 The procedure followed is that of Example 1, but using maleic acid (227.6 g) and an aqueous solution of lauryltrimethylammonium chloride (25 %, 3.576 g).
- Lauryltrimethylammonium malate is obtained as a white mass of waxy consistency, fragrant, soft, soluble in water, methanol and ethanol.
- composition lauryltrimethylammonium ion 77.60%
- Lauryltrimethylammonium malate is supplied in aqueous solution (25% w/w).
- This solution is limpid, colorless to light yellow, almost odorless, has a very bitter taste and froths copiously on agitation.
- the pH of the solution is near 6.
- reaction 2 where the suragent alcohol separated has a melting point of 24°C.
- Example 2 The procedure followed is that of Example 1, but using maleic acid (162.5 g) and an aqueous solution of cetyldimethylbenzylammonium chloride (25%, 3.696 g).
- Cetyldimethylbenzulammonium malate is obtained as a white powder of waxy consistency, soluble in water and alcohols.
- composition cetyldimethylbenzylammonium ion 84.0%
- Cetyldimethylbenzylammonium malate is supplied in aqueous solution (25% w/w). This solution is limpid, colorless to light yellow, almost odorless, has a very bitter taste and froths copiously on agitation. The pH of the solution is near 6.
- a methylene blue iodomercurate reagent paper Into an aqueous solution of cetyldimethylammonium malate, is placed a methylene blue iodomercurate reagent paper. A displacement of the iodomercurate ion is observed and the blue coloration passes into the solution.
- Example 2 The procedure followed is that of Example 1, but using maleic acid (188 g) and an aqueous solution of lauryldimethylbenzylammonium chloride (25%, 3.646 g).
- Lauryldimethylbenzylammonium malate is obtained as a white mass of waxy consistency, soluble in water and alcohols.
- the lauryldimethylbenzyl ammonium chloride is supplied in aqueous solution (25% w/w). This solution is limpid, colorless to light yellow, almost odorless, has a very bitter taste and froths copiously on agitation.
- the pH of the solution is near 6.
- a methylene blue iodomercurate reagent paper Into an aqueous solution of lauryldimethylbenzylammonium malate is placed a methylene blue iodomercurate reagent paper. A displacement of the iodomercurate anion is observed and the blue coloration passes into the solution.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7345986A FR2255282B1 (enrdf_load_stackoverflow) | 1973-12-21 | 1973-12-21 | |
| FR73.45986 | 1973-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3954846A true US3954846A (en) | 1976-05-04 |
Family
ID=9129602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/535,713 Expired - Lifetime US3954846A (en) | 1973-12-21 | 1974-12-23 | New quaternary ammonium salts of malic acid and their application in cosmetics |
Country Status (12)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4303543A (en) * | 1979-02-27 | 1981-12-01 | The Procter & Gamble Company | Method for cleansing and conditioning the skin |
| US4511513A (en) * | 1981-03-09 | 1985-04-16 | Johnson & Johnson Baby Products Company | Detergent compounds and compositions |
| US4529586A (en) * | 1980-07-11 | 1985-07-16 | Clairol Incorporated | Hair conditioning composition and process |
| US4663158A (en) * | 1979-07-02 | 1987-05-05 | Clairol Incorporated | Hair conditioning composition containing cationic polymer and amphoteric surfactant and method for use |
| US4948576A (en) * | 1983-02-18 | 1990-08-14 | Johnson & Johnson Consumer Products, Inc. | Detergent compositions |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3578667A (en) * | 1968-03-26 | 1971-05-11 | Millmaster Onyx Corp | Quaternary ammonium alicyclic carboxylates |
| US3879350A (en) * | 1973-10-26 | 1975-04-22 | Asahi Chemical Ind | Ammonium salts and polymerization of formaldehyde therewith |
-
1973
- 1973-12-21 FR FR7345986A patent/FR2255282B1/fr not_active Expired
-
1974
- 1974-12-12 NL NL7416215A patent/NL7416215A/xx not_active Application Discontinuation
- 1974-12-18 DE DE19742459993 patent/DE2459993A1/de active Pending
- 1974-12-19 SE SE7416074A patent/SE7416074L/xx unknown
- 1974-12-19 GB GB5490274A patent/GB1443639A/en not_active Expired
- 1974-12-19 CH CH1697574A patent/CH597145A5/xx not_active IP Right Cessation
- 1974-12-20 JP JP49147501A patent/JPS50111239A/ja active Pending
- 1974-12-20 BE BE151804A patent/BE823700A/xx unknown
- 1974-12-20 ES ES433206A patent/ES433206A1/es not_active Expired
- 1974-12-20 BR BR10679/74A patent/BR7410679D0/pt unknown
- 1974-12-20 IT IT54703/74A patent/IT1026121B/it active
- 1974-12-23 US US05/535,713 patent/US3954846A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3578667A (en) * | 1968-03-26 | 1971-05-11 | Millmaster Onyx Corp | Quaternary ammonium alicyclic carboxylates |
| US3879350A (en) * | 1973-10-26 | 1975-04-22 | Asahi Chemical Ind | Ammonium salts and polymerization of formaldehyde therewith |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4303543A (en) * | 1979-02-27 | 1981-12-01 | The Procter & Gamble Company | Method for cleansing and conditioning the skin |
| US4663158A (en) * | 1979-07-02 | 1987-05-05 | Clairol Incorporated | Hair conditioning composition containing cationic polymer and amphoteric surfactant and method for use |
| US4529586A (en) * | 1980-07-11 | 1985-07-16 | Clairol Incorporated | Hair conditioning composition and process |
| US4511513A (en) * | 1981-03-09 | 1985-04-16 | Johnson & Johnson Baby Products Company | Detergent compounds and compositions |
| US4948576A (en) * | 1983-02-18 | 1990-08-14 | Johnson & Johnson Consumer Products, Inc. | Detergent compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| BR7410679D0 (pt) | 1975-09-02 |
| SE7416074L (enrdf_load_stackoverflow) | 1975-06-23 |
| GB1443639A (en) | 1976-07-21 |
| JPS50111239A (enrdf_load_stackoverflow) | 1975-09-01 |
| CH597145A5 (enrdf_load_stackoverflow) | 1978-03-31 |
| NL7416215A (nl) | 1975-06-24 |
| BE823700A (fr) | 1975-06-20 |
| FR2255282B1 (enrdf_load_stackoverflow) | 1976-10-08 |
| DE2459993A1 (de) | 1975-07-03 |
| ES433206A1 (es) | 1976-12-01 |
| FR2255282A1 (enrdf_load_stackoverflow) | 1975-07-18 |
| IT1026121B (it) | 1978-09-20 |
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